Herbicidal compositions including drift retardant agents and methods of making the same

ABSTRACT

Herbicidal compositions for reducing off-site movement or drift of herbicides are described. The herbicidal compositions can include a drift retardant agent (DRA) along with at least one auxin herbicide and an emulsifying agent, such as an alkylpolysaccharide, a phosphate ester, an alkoxylated castor oil, or a combination thereof. Methods of making such composition are also described.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the benefit of and priority to U.S. ProvisionalApplication Ser. No. 62/959,429, filed Jan. 10, 2020, the entiredisclosure of which is hereby incorporated by reference.

TECHNICAL FIELD

The disclosure relates generally to herbicidal composition concentratesincluding at least one auxin herbicide, at least one drift retardantagent (DRA), and an emulsifying agent. The disclosure further relatesgenerally to methods of making such herbicidal composition concentratesas well as DRA compositions for use in the preparation of a herbicidalapplication mixture.

BACKGROUND

Auxin herbicides, such as dicamba (3,6-dichloro-2-methoxybenzoic acid)and 2,4-D (2,4-dichlorophenoxyacetic acid), are commonly used to controlauxin-susceptible plant growth on both agricultural and non-agriculturallands. Off-site movement of these herbicides has become a source ofconcern and can result in restrictions on the use of these herbicides.For example, migration of these herbicides from the application site toadjacent crop plants, such as soybeans and cotton, can occur causingcontact damage to sensitive plants. Auxin herbicide off-site movementcan occur by three primary mechanisms: physical movement or drift ofsmall particles in the spray, contamination of the sprayer, andvolatility of the herbicide after application. Monsanto has addressedvolatility by adding potassium acetate, with the trade name Vaporgrip™technology, to auxin herbicide formulations.

To address drift issues, drift retardant agents (DRAs) (also known asdrift reduction agents or drift control agents) can be included inherbicidal compositions. DRAs for herbicidal sprays can work bymodifying the size distribution of particles formed by the nozzle, forexample, by partially suppressing the formation of the smallestparticles, also known as driftable fines, which settle slowest and aremost prone to drift with the wind. Definitions of the size limit of“driftable fines” vary, but particles with a diameter below 150 μm aretypically considered susceptible to drift. There are typically two typesof DRAs. The first type of DRA is polymers, which can increase theextensional viscosity of the spray mixture. These polymers, limited incommercial practice to polyacrylamides, polyethylene oxide, and guargum, can shift the spray particle size distribution to larger diameters.While such polymers can be effective in reducing driftable fines forsome nozzles, for example, the Turbo Teejet® Induction (TTI™) nozzlefrom TeeJet and the HYPRO® Ultra Lo-Drift (ULD) nozzle, they can be lesspreferred because they can result in significantly coarser spray, whichcan provide poorer coverage, compromising weed control. Furthermore,such polymers, if incorporated into an herbicidal formulation, cangenerally result in unacceptably high viscosity.

The second type of DRA is known as “oil-type” or “emulsion-type” DRAs.As the name suggests, an oil-type DRA, largely immiscible with water,can be included in a tank formulation as an emulsion or micro-emulsion.Drift retardants of this type are available commercially as additives toa spray tank under brand names, such as Border EG (Precision Labs) andInterLock® (Winfield). These oil-type or emulsion-type DRAs can beeffective at the suppression of driftable fines, work well in a widevariety of nozzles, and can have less effect on the average particlesize of the spray; thus, providing better application coverage andherbicidal efficacy. While the use of oil-type or emulsion-type DRAs asa tank additive is common and straightforward, incorporation into anauxin herbicidal formulation remains technically challenging,particularly for producing auxin herbicidal formulations with a highload of auxin herbicide. For example, auxin herbicides, such as dicambaand 2,4-D, are typically formulated as salts in concentrated aqueoussolution. It is well known that stabilizing an emulsion in concentratedsalt solution is very difficult because emulsifiers perform poorly athigh ionic strength. Current commercial examples are Dow's Enlist Duo®and Enlist One products, which incorporate a proprietary emulsion-typeDRA into an aqueous solution of the choline salt of 2,4-D. Enlist Duo®also includes the dimethylamine salt of glyphosate. There is also apublished report from Clamant of a proprietary DRA that can beincorporated into the diglycolamine (DGA) salt of dicamba.

Accordingly, auxin herbicide compositions having a DRA incorporatedtherein for reducing drift of the herbicide are desirable, particularlyreduced-drift compositions that exhibit no significant reduction inherbicidal effectiveness relative to currently available compositions.

BRIEF SUMMARY

New and useful herbicidal compositions including a drift retardant agent(DRA) and methods of making the same are set forth in the appendedclaims. Illustrative embodiments are also provided to enable a personskilled in the art to make and use the claimed subject matter.

In one aspect, an herbicidal composition concentrate is described. Theherbicidal composition concentrate includes at least one auxinherbicide, at least one drift retardant agent, and an emulsifying agentselected from the group consisting of a phosphate ester, analkylpolysaccharide, an alkoxylated castor oil, and a combinationthereof. The at least one drift retardant agent includes one or more of:soybean oil or a methyl ester of soybean oil; a compound according ofFormula I:

wherein n is 50-250; and a compound of Formula II

wherein i+j+k=10 to 50 and r+s+t=3 to 12. In some embodiments, the auxinherbicide is selected is selected from the group consisting of dicamba,an agriculturally acceptable salt of dicamba, an agriculturallyacceptable ester of dicamba, 2,4-D, an agriculturally acceptable salt of2,4-D, an agriculturally acceptable ester of 2,4-D, and a combinationthereof. In some embodiments, the herbicidal composition furtherincludes at least one monocarboxylic acid or a monocarboxylate thereof.

In another aspect, a method of making an herbicidal compositionconcentrate is described. The method includes admixing at least oneauxin herbicide with at least one drift retardant agent, and anemulsifying agent to form the herbicidal composition concentrate. The atleast one drift retardant agent includes one or more of: soybean oil ora methyl ester of soybean oil; a compound according of Formula I:

wherein n is 50-250; and a compound of Formula II

wherein i+j+k=10 to 50 and r+s+t=3 to 12. The emulsifying agent isselected from the group consisting of a phosphate ester, analkylpolysaccharide, an alkoxylated castor oil, and a combinationthereof. In some embodiments, the auxin herbicide is selected isselected from the group consisting of dicamba, an agriculturallyacceptable salt of dicamba, an agriculturally acceptable ester ofdicamba, 2,4-D, an agriculturally acceptable salt of 2,4-D, anagriculturally acceptable ester of 2,4-D, and a combination thereof. Insome embodiments, the method further includes admixing at least onemonocarboxylic acid or a monocarboxylate thereof with the at least oneauxin herbicide, the at least one drift retardant agent, and theemulsifying agent.

In another aspect a drift retardant agent composition for use in thepreparation of a herbicidal application mixture is described. The driftretardant agent composition includes at least one drift retardant agent,and an emulsifying agent. The at least one drift retardant agentincludes soybean oil or a methyl ester of soybean oil,poly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-,and octadecanoic acid, 12-hydroxy-, homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)]. Theemulsifying agent is selected from the group consisting of a phosphateester, alkylpolysaccharide, an alkoxylated castor oil, and a combinationthereof.

Further benefits of the present invention will be apparent to oneskilled in the art from reading this patent application. The embodimentsof the invention described in the following paragraphs are intended toillustrate the invention and should not be deemed to narrow the scope ofthe invention.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1A and 1B illustrate diglycolamine (DGA) dicamba compositions withbuilt-in drift retardant agents compared to a Powermax® II/Clarity aloneand with Interlock® at 6 oz/acre (ac).

FIGS. 2A and 2B illustrate humidome volatility of Powermax® I andLiberty® tank mixtures, respectively.

FIG. 3 illustrates humidome volatility for glufosinate and dicambacompositions.

FIG. 4 illustrates humidome volatility for additional glufosinate anddicamba compositions.

DETAILED DESCRIPTION OF EXAMPLE EMBODIMENTS

The following description of example embodiments provides informationthat enables a person skilled in the art to make and use the subjectmatter set forth in the appended claims, but it may omit certain detailsalready well known in the art. The following detailed description is,therefore, to be taken as illustrative and not limiting.

The present invention provides herbicidal composition concentratescomprising an auxin herbicide wherein the compositions exhibit reduceddrift. Specifically, the compositions include, in addition to the auxinherbicide, at least one drift retardant agent (DRA), and an emulsifyingagent. The at least one drift retardant agent can include soybean oil ora methyl ester of soybean oil, poly(oxy-1,2-ethanediyl),α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-, and octadecanoic acid,12-hydroxy-, homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)]. Theemulsifying agent can be selected from the group consisting of aphosphate ester, an alkylpolysaccharide, an alkoxylated castor oil, anda combination thereof. The compositions can also include at least onemonocarboxylic acid or a monocarboxylate thereof for reducing volatilityof the herbicide upon application.

Typically, auxin herbicides, such as dicamba and 2,4-D, are formulatedas salts in concentrated aqueous solution. It is well known thatstabilizing an emulsion in a concentrated salt solution is verydifficult because emulsifiers perform poorly at high ionic strength.Additionally, inclusion of a monocarboxylic acid or a monocarboxylatethereof for reducing volatility further increases the ionic strength ofthe composition subsequently increasing the difficulty in stabilizing anemulsion of an oil type DRA and the difficulty in preventing undesirablecreaming. However, it has surprisingly been discovered that emulsionsand micro-emulsions of DRAs can be stabilized in solutions with auxinherbicides, particularly high loads of auxin herbicides in salt form(e.g., monoethanolamine (MEA) salt of dicamba) as well as compositionsincluding a monocarboxylic acid or a monocarboxylate, such potassiumacetate. It has been surprisingly discovered that the DRAs describedherein can be included with the auxins described herein by including anemulsifying agent, such as a phosphate ester, an alkylpolysaccharide, analkoxylated castor oil, or a combination thereof, to form a stableemulsion or a micro-emulsion. The compositions described herein cancontrol drift with a small amount of DRA, for example, as little asabout 0.5 oz/acre of DRA, drastically less than the 4-6 oz/acre labeledrate of Interlock™. Incorporating a reduced amount of DRA was criticalin achieving stable emulsion and micro-emulsion formulations with theDRA and auxin.

The compositions provided herein can advantageously protect againstdrift of auxins, such as dicamba and 2,4-D, when applied with manycommon nozzles per label directions. Additionally, the compositions canprovide assurance of compliance when a DRA is required, thus enhancingproduct stewardship. Incorporation of the DRA into the herbicidalcomposition concentrate also provides convenience and cost savings forgrowers and applicators compared to purchasing and adding an herbicideand a DRA separately. In various aspects, the DRAs described hereinprovide substantial suppression of fines with nozzles, such as, but notlimited to Greenleaf TurboDrop® XL (TDXL), Lechler ID, Wilger DR,Teejet® AIXR, and Teejet® TTI, without significantly increasing the meanparticle size of the spray. The compositions described herein with abuilt-in DRA enable improved spray quality with better coverage and weedcontrol.

A. Auxin Herbicide Component

The term “auxin herbicide” refers to an herbicide that functions as amimic of an auxin plant growth hormone, thereby affecting plant growthregulation. Examples of auxin herbicides that are suitable for use inthe herbicidal compositions of the present invention include, withoutlimitation, benzoic acid herbicides, phenoxy herbicides, pyridinecarboxylic acid herbicides, pyridine oxy herbicides, pyrimidine carboxyherbicides, quinoline carboxylic acid herbicides, and benzothiazoleherbicides.

Examples of auxin herbicides include, but are not limited to:3,6-dichloro-2-methoxybenzoic acid (dicamba); 2,4-dichlorophenoxyaceticacid (2,4-D); 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB);dichloroprop; 2-methyl-4-chlorophenoxyacetic acid (MCPA);4-(4-chloro-2-methylphenoxy)butanoic acid (MCPB); 4-chlorophenoxyaceticacid; 2,4,5-trichlorophenoxyacetic acid (2,4,5-T); aminopyralid;clopyralid; fluroxypyr; triclopyr; mecoprop; picloram; quinclorac;aminocyclopyrachlor; benazolin; halauxifen; fluorpyrauxifen; methyl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylicacid;4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylicacid; benzyl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylicacid; methyl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylicacid; methyl4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylicacid; methyl4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylicacid; methyl6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylicacid; butyl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylicacids, including salts and esters thereof; racemic mixtures and resolvedisomers thereof; and combinations thereof.

In any embodiment, the herbicidal composition concentrate can includedicamba, or an agriculturally acceptable salt or ester thereof. Examplesof suitable dicamba salts include, but are not limited toN,N-bis-[aminopropyl]methylamine, monoethanolamine (MEA), dimethylamine(e.g., BANVEL®, ORACLE®, etc.), isopropylamine, triethanolamine (TEA),diglycolamine (e.g., CLARITY®, VANQUISH®, etc.), potassium, and sodiumsalts, and combinations thereof. Commercially available sources ofdicamba, and its agriculturally acceptable salts, include those productssold under the trade names BANVEL®, CLARITY®, DIABLO®, DISTINCT,ORACLE®, VANQUISH®, and VISION®.

In any embodiment, the herbicidal composition concentrate can include anagriculturally acceptable dicamba salt, wherein the salt is selectedfrom the group consisting of N,N-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine, apotassium salt, and a sodium salt, and combinations thereof.

Throughout the remainder of the description of the invention, wherereference is made to dicamba, or an agriculturally acceptable salt orester thereof, one skilled in the art will understand that theprinciples of the present invention apply to auxin herbicides generally,including those described above, and that the present invention is notlimited to herbicidal compositions containing dicamba, or anagriculturally acceptable salt or ester thereof.

Additionally or alternatively, the herbicidal composition concentratecan include 2,4-D, or an agriculturally acceptable salt or esterthereof. Examples of suitable 2,4-D salts include, but are not limitedto the choline, dimethylamine, triethanolamine, and isopropylaminesalts, and combinations thereof. Examples of suitable 2,4-D estersinclude, but are not limited to methyl, ethyl, propyl, butyl (2,4-DB),and isooctyl esters, and combinations thereof. Commercially availablesources of 2,4-D, and its agriculturally acceptable salts and esters,include those products sold under the trade names BARRAGE®, FORMULA 40®,OPT-AMINE®, and WEEDAR 64®.

Additionally or alternatively, the herbicidal composition concentratecan include an agriculturally acceptable 2,4-D salt, wherein the salt isselected from the group consisting of choline, dimethylamine,triethanolamine, and isopropylamine salts, and combinations thereof.

Additionally or alternatively, the herbicidal composition concentratecan include an agriculturally acceptable 2,4-D ester, wherein the esteris selected from the group consisting of butyl (i.e., 2,4-DB) andisooctyl esters, and combinations thereof.

Additionally or alternatively, the herbicidal composition concentratecan include at least two auxin herbicides, for example, dicamba, or anagriculturally acceptable salt or ester thereof, and 2,4-D, or anagriculturally acceptable salt or ester thereof.

Additionally or alternatively, the herbicidal composition concentratecan include an agriculturally acceptable auxin herbicide salt (such as adicamba salt, a 2,4-D salt, and/or a 2,4-DB salt) that is an ionicliquid as described in published application US 2013/0109572, i.e., asalt that is a liquid at a temperature at or below about 150° C. Theentire text of US 2013/0109572 is incorporated by reference into thisapplication.

B. Drift Retardant Agent (DRA) Component

In various aspects, the DRA may include one or more of an oil or anester thereof, a poly(ethyleneglycol)monooleate, and a polymer.

The oil or an ester thereof may be present in the DRA in amount, byweight of the DRA, of greater than or equal to about 50%, greater thanor equal to about 60%, greater than or equal to about 70%, greater thanor equal to about 80%, greater than or equal to about 85%, greater thanor equal to about 90%, or about 95%; or from about 50% to about 95%,about 70% to about 95%, about 80% to about 95%, about 85% to about 95%,or about 90% to about 95%. The poly(ethyleneglycol)monooleate may bepresent in the DRA in amount, by weight of the DRA, of greater than orequal to about 0.10%, greater than or equal to about 0.25%, greater thanor equal to about 0.5%, greater than or equal to about 1%, greater thanor equal to about 5%, or about 10%; from about 0.1% to about 10%, about0.25% to about 10%, about 0.5% to about 10%, or about 1% to about 5%.The polymer may be present in the DRA in amount, by weight of the DRA,of greater than or equal to about 1%, greater than or equal to about 3%,greater than or equal to about 5%, greater than or equal to about 10%,greater than or equal to about 20%, greater than or equal to about 30%,greater than or equal to about 40%, or about 50%; or from about 1% toabout 50%, about 3% to about 50%, about 5% to about 40%, or about 10% toabout 30%.

A suitable oil includes, but is not limited to soybean oil (e.g., CASRegistry Number 8001-22-7) or an ester of soybean oil, for example, amethyl ester of soybean oil (e.g., CAS Registry Number 67784-80-9).Suitable poly(ethyleneglycol)monooleates include, but are not limited tocompounds of Formula I:

where n is 50-250. In some embodiments, thepoly(ethyleneglycol)monooleate can be poly(oxy-1,2-ethanediyl),α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- (e.g., CAS Registry Number9004-96-0).

Suitable polymers include, but are not limited to compounds of FormulaII:

wherein i+j+k=10 to 50 or 20 to 35 and r+s+t=3 to 12 or 4 to 8. In anyembodiment, each of i, j, and k independently can be an integer fromzero to 50, an integer from zero to 35, an integer from zero to 20, aninteger from zero to 10, an integer from 1 to 50, an integer from 1 to35, an integer from 1 to 20, an integer from 1 to 10, an integer from 5to 50, an integer from 5 to 35, an integer from 5 to 20, or an integerfrom 5 to 10. For example, i can be 1, j can be 5, and k can be 4; or ican be zero, j can be 10, and k can be 12, and so on. In any embodiment,each of r, s, and t independently can be an integer from zero to 12, aninteger from zero to 8, an integer from zero to 4, an integer from zeroto 3, an integer from 1 to 12, an integer from 1 to 8, an integer from 1to 4, an integer from 1 to 3, an integer from 2 to 12, an integer from 2to 8, an integer from 2 to 4, or an integer from 2 to 3. For example, rcan be 1, s can be 1, and t can be 1; or r can be zero, s can be 3, andt can be 5, and so on. In some embodiments, the polymer can beoctadecanoic acid, 12-hydroxy-, homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)] (e.g., CASRegistry Number 1939051-18-9).C. Emulsifying Agent Component

While it is known that herbicidal activity of herbicides, such asglyphosate, can be enhanced by certain cationic surfactants, forexample, tallowamine ethoxylates, it was found that such surfactants areincompatible with the compositions including a combination of an auxinherbicide (e.g., dicamba) and a DRA as described herein, and optionally,a monocarboxylic acid or the monocarboxylate thereof (e.g., potassiumacetate). However, it has been surprisingly found that emulsifyingagents, such as a phosphate ester, an alkylpolysaccharide, analkoxylated castor oil, or a combination thereof can be included in thecompositions described herein and stabilize emulsions or micro-emulsionsof the DRA and the auxin herbicide and prevent creaming of the DRA. Asused herein “emulsifying agent” is intended to encompass surfactants andsolvents. Additionally, the emulsifying agents described herein canprovide a comparable level of glyphosate activity against weeds. Thus,the composition concentrates described herein can control drift andprovide an effective combination of two herbicides, for example, dicambaand glyphosate or dicamba and glufosinate, in a convenient, stable,concentrated mixture, optionally including a monocarboxylic acid or themonocarboxylate thereof (e.g., potassium acetate, such as Vaporgrip™Technology) to control volatility of dicamba.

In any embodiment, the emulsifying agent may be a phosphate ester.Examples of suitable phosphate esters include, but are not limited toalkoxylated phosphate esters of fatty acids. The alkoxylation mayinclude alkoxy chain of any length. For example, polyethylene oxide orpolypropylene oxide. Examples of said esters include polyethylene glycoloctyl phosphate, polyethylene glycol isotridecyl phosphate, polyethyleneglycol cetearyl phosphate, polyethylene glycol decyl phosphate,polyethylene glycol oleyl phosphate, polyethylene glycol polypropyleneglycol cetyl phosphate, polyethylene glycol tridecyl phosphate, andpolyethylene glycol isotridecyl phosphate. Non-limiting examples ofcommercially available phosphate esters include Stepfac® 8182, Stepfac®8181 and Stepfac® 8180, Toximul® TAABS-8 and Toximul® TAABS-5.

Additionally or alternatively, the emulsifying agent may be analkylpolysaccharide. Examples of suitable alkylpolysaccharide include,but are not limited to compounds of Formula (1):R¹¹—O-(sug)_(u)  Formula (1)

wherein R¹¹ is a straight or branched chain substituted or unsubstitutedhydrocarbyl selected from alkyl, alkenyl, alkylphenyl, alkenylphenylhaving from about 4 to about 22 carbon atoms for from about 4 to 18carbon atoms. The sug moiety is a saccharide residue, and may be an openor cyclic (i.e., pyranose) structure. The saccharide may be amonosaccharide having 5 or 6 carbon atoms, a disaccharide, anoligosaccharide or a polysaccharide. Examples of suitable saccharidemoieties, including their corresponding pyranose form, include ribose,xylose, arabinose, glucose, galactose, mannose, telose, gulose, allose,altrose, idose, lyxose, ribulose, sorbose (sorbitan), fructose, andmixtures thereof. Examples of suitable disaccharides include maltose,lactose and sucrose. Disaccharides, oligosaccharides and polysaccharidescan be a combination of two or more identical saccharides, for examplemaltose (two glucoses) or two or more different saccharides, for examplesucrose (a combination of glucose and fructose). The degree ofpolymerization, u, is an average number from 1 to about 10, from 1 toabout 8, from 1 to about 5, from 1 to about 3, and from 1 to about 2.

In various embodiments, the alkylpolysaccharide may be analkylpolyglucoside (APG) surfactant of Formula (1) wherein: R¹¹ is abranched or straight chain alkyl group preferably having from 4 to 22carbon atoms or from 8 to 18 carbon atoms, or a mixture of alkyl groupshaving an average value within the given range; sug is a glucose residue(e.g., a glucoside); and u is from 1 to about 5, and more preferablyfrom 1 to about 3. In various embodiments, the emulsifying agentcomponent comprises an APG of Formula (1) wherein R¹¹ is a branched orstraight chain alkyl group having from 8 to 10 carbon atoms or a mixtureof alkyl groups having an average value within the given range and u isfrom 1 to about 3.

Non-limiting examples of commercially available alkylpolyglucosidesinclude, for example, APG®, AGNIQUE®, or AGRIMUL® surfactants from BASFInc., for example, Agnique PG 264, Agnique PG 8105, and Agnique 8107.

Additionally or alternatively, the emulsifying agent may be analkoxylated castor oil, for example an ethoxylated castor oil or aproproxylated castor oil. Alkoxylated castor oil can be prepared byreaction of castor oil or hydrogenated castor oil with ethylene oxide,propylene oxide, ethylene glycol, or propylene glycol. Examples of asuitable alkoxylated castor oil include, but are not limited toStepantex® CO-40 (40 EO), Toximul® 8242, both available from StepanChemical Company, and Cirrasol™ G-1292 (25 EO) available from Croda Inc.Additional non-limiting examples include Toximul® 8243 and Toximul®8244. Other suitable examples may include Emulpon CO-550, CO-360, CO-200from AkzoNobel Nouryon and Surfom R 360 and R 540 from Oxiteno.

Additionally or alternatively, the emulsifying agent may be analkoxylated fatty acid ester. Non-limiting examples of such estersinclude ethoxylated methyl esters of fatty acids, such as commerciallyavailable Agnique® ME 818-5. Other suitable examples may includeBreak-Thru® EM V20.

D. Monocarboxylic Acid/Monocarboxylate Component

“Monocarboxylic acid” refers to a hydrocarbon or substituted hydrocarboncontaining only one carboxy functional group (i.e., R¹—C(O)OH).“Monocarboxylate” refers to a salt (i.e., R¹—C(O)OM wherein M is anagriculturally acceptable cation). In one embodiment, the compositioncomprises at least one monocarboxylate salt, which in aqueouscompositions may be present, in whole or in part, in dissociated form asa monocarboxylate anion and the corresponding cation.

Representative monocarboxylic acids and monocarboxylates generallycomprise a hydrocarbon or unsubstituted hydrocarbon selected from, forexample, unsubstituted or substituted, straight or branched chain alkyl(e.g., C₁-C₂₀ alkyl such as methyl, ethyl, n-propyl, isopropyl, etc.);unsubstituted or substituted, straight or branched chain alkenyl (e.g.,C₂-C₂₀ alkyl such as ethenyl, n-propenyl, isopropenyl, etc.);unsubstituted or substituted aryl (e.g., phenyl, hydroxyphenyl, etc.);or unsubstituted or substituted arylalkyl (e.g., benzyl). In oneembodiment, the monocarboxylic acid is selected from the groupconsisting of formic acid, acetic acid, propionic acid, and benzoicacid. In another embodiment, the monocarboxylate salt is selected fromthe group consisting of formate salts, acetate salts, propionate salts,and benzoate salts.

In one embodiment, the herbicidal composition comprises amonocarboxylate salt having the formula R¹—C(O)OM, wherein R¹ isunsubstituted or substituted C₁-C₁₀ alkyl and M is a non-amine,agriculturally acceptable cation. In another embodiment, the herbicidalcomposition comprises a monocarboxylate salt having the formulaR¹—C(O)OM, wherein R¹ is unsubstituted C₁-C₆ alkyl and M is an alkalimetal salt. In another embodiment, the herbicidal composition comprisesa monocarboxylate salt having the formula R¹—C(O)OM, wherein R¹ isunsubstituted C₁-C₃ alkyl and M is an alkali metal salt selected fromsodium and potassium. In another embodiment, the monocarboxylate salt ispotassium acetate. In another embodiment, the monocarboxylate salt issodium acetate.

In any embodiment, the herbicidal composition concentrates describedherein can have a pH that is preferably equal to or higher than the aciddissociation constant (pKa) of the monocarboxylic acid, if present inthe composition. For example, the herbicidal composition concentratescan include acetic acid (which has a pKa of about 4.8) and have a pHequal to or greater than about 4.8.

E. Alkali Metal Phosphate/Alkali Metal Carbonate

The herbicidal composition concentrates optionally may further includean alkali metal phosphate such as dipotassium phosphate. Dipotassiumphosphate, for example, can provide additional buffering and/orwater-conditioning for aqueous herbicidal compositions of the presentinvention. Dipotassium phosphate is particularly effective as areplacement for ammonium sulfate in herbicidal composition applicationmixtures prepared using hard water.

Additionally or alternatively, the herbicidal composition concentratesoptionally may further include an alkali metal carbonate, such aspotassium carbonate, to provide additional buffering and/orwater-conditioning for aqueous herbicidal compositions of the presentinvention.

F. Non-Herbicide Additives

The herbicidal composition concentrates optionally may further includeconventional additives, such as further surfactants, safeners,solubility enhancing agents, thickening agents, flow enhancers,foam-moderating agents, freeze protectants, UV protectants,preservatives, antimicrobials, and/or other additives that are necessaryor desirable to improve the performance, crop safety, or handling of thecomposition.

In any embodiment, the herbicidal composition concentrate can includeless than about 10 ppm of ammonium sulfate. In another embodiment, theherbicidal composition concentrate does not include ammonium sulfate.

In any embodiment, the herbicidal composition concentrate does notinclude an acid other than a monocarboxylic acid.

G. Further Herbicide Components

The herbicidal composition concentrates optionally may include at leastone further herbicide. Representative examples of a further herbicideinclude, but are not limited to hydroxyphenylpyruvate dioxygenase (HPPD)inhibitors, acetyl-CoA carboxylase (ACCase) inhibitors, acetolactatesynthase (ALS) inhibitors, acetohydroxy acid synthase (AHAS) inhibitors,photosystem II (PS II) inhibitors, photosystem I (PS I) inhibitors,protoporphyrinogen oxidase (PPO or Protox) inhibitors, carotenoidbiosynthesis inhibitors, enolpyruvyl shikimate-3-phosphate (EPSP)synthase inhibitor, glutamine synthetase inhibitor, dihydropteroatesynthetase inhibitor, mitosis inhibitors, nucleic acid inhibitors,cellulose inhibitors, oxidative phosphorylation uncouplers,dihydropteroate synthase inhibitors, fatty acid and lipid biosynthesisinhibitors, auxin transport inhibitors, salts and esters thereof,racemic mixtures and resolved isomers thereof, and mixtures thereof;salts and esters thereof; racemic mixtures and resolved isomers thereof;and combinations thereof.

Application mixtures can be prepared by diluting aqueous herbicidalconcentrate compositions as described herein. Additional herbicides canbe “tank mixed” with the application mixtures prepared from the aqueousherbicidal concentrate compositions described herein.

Examples of herbicides within these classes of further herbicides areprovided below. Where an herbicide is referenced generically herein byname, unless otherwise restricted, that herbicide includes allcommercially available forms known in the art such as salts, esters,free acids and free bases, as well as stereoisomers thereof.

Representative examples of HPPD inhibitors include, but are not limitedto aclonifen, amitrole, beflubutamid, benzofenap, clomazone,diflufenican, fluridone, flurochloridone, flurtamone, isoxachlortole,isoxaflutole, mesotrione, norflurazon, picolinafen, pyrazolynate,pyrazoxyfen, sulcotrione, tembotrione, topramezone, tolpyralate,tefuryltrione, salts and esters thereof, and mixtures thereof.

Representative examples of ACCase inhibitors include, but are notlimited to alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden,sethoxydim, tepraloxydim and tralkoxydim, salts and esters thereof, andmixtures thereof. Another group of ACCase inhibitors includechlorazifop, clodinafop, clofop, cyhalofop, diclofop, diclofop-methyl,fenoxaprop, fenthiaprop, fluazifop, haloxyfop, isoxapyrifop, metamifop,propaquizafop, quizalofop and trifop, salts and esters thereof, andmixtures thereof. ACCase inhibitors also include mixtures of one or more“dims” and one or more “fops”, salts and esters thereof.

Representative examples of ALS or AHAS inhibitors include, but are notlimited to amidosulfuron, azimsulfruon, bensulfuron-methyl,bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florazulam, flucarbazone,flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, foramsulfuron,halosulfuron-methyl, imazamethabenz, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron, metsulfuron-methyl,nicosulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium,prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrithiobac,rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone,thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuronand triflusulfuron-methyl, salts and esters thereof, and mixturesthereof.

Representative examples of photosystem I inhibitors include, but are notlimited to diquat and paraquat, salts and esters thereof, and mixturesthereof. Representative examples of photosystem II inhibitors include,but are not limited to ametryn, amicarbazone, atrazine, bentazon,bromacil, bromoxynil, chlorotoluron, cyanazine, desmedipham, desmetryn,dimefuron, diuron, fluometuron, hexazinone, ioxynil, isoproturon,linuron, metamitron, methibenzuron, metoxuron, metribuzin, monolinuron,phenmedipham, prometon, prometryn, propanil, pyrazon, pyridate, siduron,simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazineand trietazine, salts and esters thereof, and mixtures thereof.

Representative examples of PPO inhibitors include, but are not limitedto Diphenylethers (acifluorfen-sodium, bifenox, chlomethoxyfen,chlornitrofen, ethoxyfen-ethyl, fluoroglycofen-ethyl, fomesafen,lactofen, oxyfluorfen), N-phenylphthalimides (cinidon-ethyl, fumiclorac,flumiclorac-pentyl, flumioxazin), oxadiazoles (oxadiargyl, oxadiazon),oxazolidinediones (pentoxazone), phenylpyrazoles (fluazolate,pyraflufen-ethyl), pyrimidindiones (benzfendizone, butafenacil,saflufenacil, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate),thiadiazoles (fluthiacet-methyl, thidiazimin), triazinone(trifludimoxazin), triazolinones (azafenidin, carfentrazone-ethyl,sulfentrazone) and others (flufenpyr-ethyl, profluazol, pyraclonil).

Representative examples of carotenoid biosynthesis inhibitors include,but are not limited to aclonifen, amitrole, diflufenican, mesotrione,and sulcotrione.

A representative example of an EPSP inhibitor includes, but is notlimited to N-phosphonomethyl glycine (glyphosate).

A representative example of a glutamine synthetase inhibitor includes,but is not limited to glufosinate.

A representative example of a dihydropteroate synthetase inhibitorincludes, but is not limited to asulam.

Representative examples of mitosis inhibitors include, but are notlimited to acetochlor, alachlor, dithiopyr, S-metolachlor, andthiazopyr.

Representative examples of nucleic acid inhibitors include, but are notlimited to difenzoquat, fosamine, metham, and pelargonic acid.

In any embodiment, the herbicidal composition concentrate furtherincludes a further herbicide selected from the group consisting ofacetochlor, glyphosate, glufosinate, flumioxazin, fomesafen, andagriculturally acceptable salts thereof.

In one embodiment, the herbicidal composition concentrate furtherincludes glyphosate, or an agriculturally acceptable salt thereof.Suitable glyphosate salts include, for example, the ammonium,diammonium, dimethylammonium, monoethanolamine, isopropylamine, andpotassium salts, and combinations thereof. In any embodiment, theglyphosate salts are selected from the group consisting ofmonoethanolamine, isopropylamine, and potassium salts, and combinationsthereof.

In any embodiment, the herbicidal composition concentrate furtherincludes glufosinate, or an agriculturally acceptable salt thereof.

In any embodiment, the herbicidal composition concentrate includesdicamba, or an agriculturally acceptable salt or ester thereof, andglyphosate, or an agriculturally acceptable salt thereof. Additionallyor alternatively, the herbicidal composition concentrate includesdicamba, or an agriculturally acceptable salt thereof; glyphosate, or anagriculturally acceptable salt thereof; and a non-amine, agriculturallyacceptable acetate salt. Commercially available sources of glyphosate,and its agriculturally acceptable salts, include those products soldunder the trade names DURANGO® DMA®, HONCHO PLUS®, ROUNDUP POWERMAX®,ROUNDUP WEATHERMAX®, TRAXION®, and TOUCHDOWN®.

Additionally or alternatively, the herbicidal composition concentrateincludes 2,4-D, or an agriculturally acceptable salt or ester thereof,and glyphosate, or an agriculturally acceptable salt thereof.Additionally or alternatively, the herbicidal composition concentrateincludes 2,4-D, or an agriculturally acceptable salt or ester thereof;glyphosate, or an agriculturally acceptable salt thereof; and anon-amine, agriculturally acceptable acetate salt.

In any embodiment, the herbicidal composition concentrate includesdicamba, or an agriculturally acceptable salt or ester thereof, andglufosinate, or an agriculturally acceptable salt thereof. Additionallyor alternatively, the herbicidal composition concentrate includes 2,4-D,or an agriculturally acceptable salt or ester thereof, and glufosinate,or an agriculturally acceptable salt thereof.

In any embodiment, the herbicidal composition concentrate includes anagriculturally acceptable non-auxin herbicide salt (such as a glyphosatesalt) that is an ionic liquid as described in published applicationUS2013/0109572, i.e., a salt that is a liquid at a temperature at orbelow about 150° C.

H. Component Loading

1. Herbicide Loading:

The herbicidal composition concentrate described herein can be dilutedwith water prior to application. Concentrated herbicidal compositions asdescribed herein typically can include on an acid equivalent basis (a.e.or ae), for example, from about 120 to about 600 g a.e./L, from about300 to about 600 g a.e./L, from about 350 to about 600 g a.e./L, fromabout 400 to about 600 g a.e./L, from about 450 to about 600 g a.e./L,or from about 500 to about 600 g a.e./L total herbicide loading. As usedherein, the term “total herbicide loading” encompasses a herbicideloading when only one herbicide is present in the composition, forexample, one auxin herbicide or one non-auxin herbicide, as well as thetotal when one or more herbicides are present, for example, two auxinherbicides or an auxin herbicide and a non-auxin herbicide. Additionalexamples of representative total herbicide loading include about 120,150, 200, 250, 300, 350, 400, 450, 500, 550, and 600 g a.e./L, andranges thereof (i.e., from about 120 to about 150 g a.e./L, from about150 to about 200 g a.e./L, from about 200 to about 250 g a.e./L, fromabout 250 to about 300 g a.e./L, from about 300 to about 350 g a.e./L,from about 350 to about 400 g a.e./L from about 400 to about 450 ga.e./L, from about 450 to about 500 g a.e./L, from about 500 to about550 g a.e./L, from about 550 to about 600 g a.e./L total herbicideloading).

In any embodiment, the herbicidal composition can be a liquidconcentrate containing, for example, a total amount (acid equivalentweight) of herbicide, by weight of the composition concentrate, ofgreater than or equal to about 5%, greater than or equal to about 10%,greater than or equal to about 15%, greater than or equal to about 20%,greater than or equal to about 30%, greater than or equal to about 40%,greater than or equal to about 50%, greater than or equal to about 60%,or about 70%. Additionally or alternatively, the herbicidal compositionis a liquid concentrate containing, for example, a total amount (acidequivalent weight) of herbicide, by weight of the compositionconcentrate, from about 5% to about 70%, about 5% to about 60%, about 5%to about 50%, about 10% to about 40%, about 10% to about 30%, or aboutor about 10% to about 20%.

In herbicidal compositions concentrates including an auxin herbicide anda non-auxin herbicide, the weight ratio on an acid equivalent basis ofthe auxin herbicide to the non-auxin herbicide is typically no greaterthan about 50:1, for example, about 50:1, 25:1, 10:1, 5:1, 3:1, 2:1,1:1, 1:2, 1:3, 1:5, about 1:10, or ranges thereof such as from about50:1 to about 1:10, from about 50:1 to about 1:5, from about 50:1 toabout 1:1, from about 50:1 to about 3:1, from about 50:1 to about 5:1,from about 50:1 to about 10:1, from about 25:1 to about 1:1, or fromabout 25:1 to about 3:1.

In a particular embodiment, the herbicidal composition concentrate caninclude an auxin herbicide in an amount (acid equivalent weight), byweight of the composition concentrate, of about 5% to about 70%, about5% to about 60%, about 5% to about 50%, about 10% to about 40%, about10% to about 30%, or about or about 10% to about 20%, and non-auxinherbicide in an amount (acid equivalent weight), by weight of thecomposition concentrate, of about 10% to about 70%, about 15% to about60%, about 15% to about 50%, or about 20% to about 40%.

For any given auxin herbicide, one skilled in the art can readilydetermine using routine experimentation a minimum concentration of auxinherbicide and a minimum ratio of auxin herbicide to any additional auxinherbicides and/or non-auxin herbicides contained in the herbicidalcomposition that is desirable for the intended application.

2. Drift Retardant Agent (DRA) Loading:

In any embodiment, the at least one DRA as described herein may bepresent in the composition concentrate, by weight of the compositionconcentrate, in a total DRA loading of greater than or equal to about1%, greater than or equal to about 2%, greater than or equal to about5%, greater than or equal to about 8%, greater than or equal to about10%, greater than or equal to about 12%, greater than or equal to about15%, or about 20%. As used herein, the term “total DRA loading”encompasses a DRA loading when only one DRA is present in thecomposition as well as the total when one or more DRAs are present.Additionally or alternatively, the at least one DRA may be present inthe composition concentrate, by weight of the composition concentrate,in a total DRA loading of about 1% to about 20%, about 1% to about 15%,about 2% to about 12%, about 2% to about 10%, or about or about 5% toabout 10%.

3. Emulsifying Agent Total Loading

In any embodiment, the emulsifying agent as described herein may bepresent in the composition concentrate, by weight of the compositionconcentrate, in a total emulsifying agent loading of greater than orequal to about 1 wt. %, greater than or equal to about 2 wt. %, greaterthan or equal to about 3 wt. %, greater than or equal to about 4 wt. %,greater than or equal to about 5 wt. %, greater than or equal to about 6wt. %, greater than or equal to about 7 wt. %, greater than or equal toabout 8 wt. %, greater than or equal to about 9 wt. %, greater than orequal to about 10 wt. %, greater than or equal to about 12 wt. %,greater than or equal to about 15 wt. %, greater than or equal to about20 wt. %, greater than or equal to about 25 wt. %, greater than or equalto about 25 wt. %, or about 30 wt. %. As used herein, the term “totalemulsifying agent loading” encompasses a emulsifying agent loading whenonly one emulsifying agent is present in the composition as well as thetotal when one or more emulsifying agents are present. Additionally oralternatively, the emulsifying agent may be present in the compositionconcentrate, by weight of the composition concentrate, in a totalemulsifying agent loading of about 1 wt. % to about 30% wt. %, about 1wt. % to about 25% wt. %, about 2 wt. % to about 25 wt. %, about 3 wt. %to about 25 wt. %, about 4 wt. % to about 25 wt. %, about 5 wt. % toabout 25 wt. %, about 5 wt. % to about 20 wt. %, about 10 wt. % to about20 wt. %, about 15 wt. % to about 20 wt. %, or about 10 wt. % to about15 wt. %.

4. Monocarboxylic Acid/Monocarboxylate Loading:

In any embodiment, the herbicidal composition concentrate may include asingle monocarboxylic acid, or monocarboxylate thereof, or a mixture oftwo or more monocarboxylic acids, or monocarboxylates thereof.

In various embodiments, the concentration of volatilized auxin herbicidein the vapor phase surrounding a herbicidal composition comprising anauxin herbicide and a monocarboxylic acid, or monocarboxylate thereof,is less than about 90%, 80%, 70%, 60%, 50%, 40%, 30%, 20%, 10%, or 5% ofthe concentration of volatilized auxin herbicide in the vapor phasesurrounding the reference composition lacking the monocarboxylate.

The monocarboxylic acid or monocarboxylate loading of the herbicidalcomposition generally can depend upon the auxin herbicide loading of theherbicidal composition, the salt form of the auxin herbicide, and theproperties of any other components of the herbicidal composition, andwill be an amount sufficient to reduce the volatility of the auxinherbicide relative to a reference composition lacking the monocarboxylicacid or monocarboxylate, but otherwise having the same composition. Forexample, the monoethanolamine and diglycolamine salts of dicamba areless volatile than the dimethylamine and isopropylamine salts of dicambaand the loading required for the less volatile salts may be less thanthe loading required for the more volatile salts. In addition, theloading of the monocarboxylic acid, or monocarboxylate thereof, can varywith the specific combination of auxin herbicide, optional non-auxinherbicide, and monocarboxylic acid, or monocarboxylate thereof.

In the herbicidal composition concentrates described herein, the molarratio of the auxin herbicide to the monocarboxylic acid, ormonocarboxylate thereof, is typically no less than about 1:10 and nogreater than about 10:1. Representative molar ratios of auxin herbicideacid equivalent (a.e.) to total monocarboxylic acid, or monocarboxylatethereof, are, for example, from 1:10 to about 10:1, from about 3:10 toabout 10:1, from about 1:5 to about 5:1, and from about 3:1 to about1:3. In any embodiment, the molar ratio of auxin herbicide tomonocarboxylic acid, or monocarboxylate thereof, is about 2:1 to about1:2. In any embodiment, the molar ratio of auxin herbicide tomonocarboxylic acid, or monocarboxylate thereof, is about 1:1.

In any embodiment, the herbicidal composition concentrates can containan amount (acid equivalent weight) of the monocarboxylic acid, ormonocarboxylate thereof, by weight of the concentrate, from about 0.25%to about 35%, about 5% to about 30%, or about 5% to about 20%.

5. Alkali Metal Phosphate/Alkali Metal Carbonate Loading

When the herbicidal composition concentrate includes an alkali metalphosphate, such as dipotassium phosphate, the molar ratio of the alkalimetal phosphate to the monocarboxylic acid, or monocarboxylate thereof,can range, for example, from about 1:5 to about 5:1, from about 3:1 toabout 1:3, or from about 2:1 to about 1:2. In any embodiment, the molarratio of alkali metal phosphate to monocarboxylic acid, ormonocarboxylate thereof, is about 1:1.

When the herbicidal composition concentrate includes an alkali metalcarbonate, such as potassium carbonate, the molar ratio of the alkalimetal carbonate to the monocarboxylic acid, or monocarboxylate thereof,can range, for example, from about 1:5 to about 5:1, from about 3:1 toabout 1:3, or from about 2:1 to about 1:2. In any embodiment, the molarratio of alkali metal carbonate to monocarboxylic acid, ormonocarboxylate thereof, is about 1:1.

I. Methods of Making an Herbicidal Composition Concentrate

Methods of making herbicidal composition concentrate as described hereinare also provided. The herbicidal composition concentrate formed can bean emulsion or a micro-emulsion. The method may include admixing atleast one auxin herbicide as described herein with at least one driftretardant agent (DRA) as described herein and an emulsifying agent asdescribed herein to form the herbicidal composition concentrate. Forexample, the DRA can include soybean oil or a methyl ester of soybeanoil, poly(oxy-1,2-ethanediyl),α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-, and octadecanoic acid,12-hydroxy-, homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)]. The DRAcan include soybean oil or a methyl ester of soybean oil in an amount ofabout 80% to about 95% by weight of the DRA, poly(oxy-1,2-ethanediyl),α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- in an amount of about 0.25%to about 10% by weight of the DRA, and octadecanoic acid, 12-hydroxy-,homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)] in anamount of about 3% to about 50% by weight of the DRA.

The emulsifying agent can be selected from the group consisting of aphosphate ester, an alkylpolysaccharide, an alkoxylated castor oil, anda combination thereof. For example, the at least one auxin herbicide canbe selected from the group consisting of dicamba, an agriculturallyacceptable salt of dicamba (e.g., N,N-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine, apotassium salt, and a sodium salt, and a combination thereof), anagriculturally acceptable ester of dicamba, 2,4-D, an agriculturallyacceptable salt of 2,4-D, an agriculturally acceptable ester of 2,4-D,and a combination thereof.

The total herbicide loading of the composition concentrate can be asdescribed herein, for example, an amount (acid equivalent weight) ofabout 5% to about 50% by weight of the composition concentrate. Thetotal DRA loading of the composition concentrate can be as describedherein, for example, an amount of about 2% to about 10% by weight of thecomposition concentrate. The total emulsifying agent loading of thecomposition concentrate can be as described herein, for example, anamount of about 1% to about 20% by weight of the compositionconcentrate.

In any embodiment, the method may further include admixing the at leastauxin herbicide with water to form an aqueous solution prior to admixingwith the at least one drift retardant agent and the emulsifying agent.Additionally or alternatively, the method may further include admixingat least one monocarboxylic acid (e.g., acetic acid) or amonocarboxylate thereof (e.g., potassium acetate) with the at least oneauxin herbicide, the at least one drift retardant agent, and theemulsifying agent. In any embodiment, the herbicidal compositionconcentrate can contain an amount (acid equivalent weight) of themonocarboxylic acid, or monocarboxylate thereof, by weight of theconcentrate, as described herein, for example, about 5% to about 30%and/or a molar ratio of the at least one monocarboxylic acid or themonocarboxylate thereof to the auxin herbicide as described herein, forexample, from about 1:10 to about 10:1.

Additionally or alternatively, the method may further comprise mixing atleast one further herbicide (e.g., glyphosate, an agriculturallyacceptable salt of glyphosate, glufosinate, an agriculturally acceptablesalt of glufosinate, and a combination thereof) with the at least oneauxin herbicide, the at least one DRA, and the emulsifying agent.Optionally, an antifoam agent may be added to suppress formation of foamwhile mixing. A suitable antifoam agent includes, but is not limited toa silicone antifoam agent, for example, SAG 1572 available fromMomentive. The further herbicide can be present in the herbicidalcomposition concentrate in an amount (acid equivalent weight) asdescribed herein, for example, about 15% to about 60% by weight of thecomposition.

J. Drift Retardant Agent (DRA) Composition

A drift retardant agent (DRA) composition for use in the preparation ofan herbicidal application mixture is also provided herein. The DRAcomposition can include at least one DRA as described herein. and anemulsifying agent as described herein. For example, the DRA can includesoybean oil or a methyl ester of soybean oil, poly(oxy-1,2-ethanediyl),α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-, and octadecanoic acid,12-hydroxy-, homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)]. Theemulsifying agent can be, for example, a phosphate ester, analkylpolysaccharide, an alkoxylated castor oil, or a combinationthereof. It is contemplated herein that this DRA composition can beadmixed with further components, such as the herbicides described hereinand/or the monocarboxylic acid/monocarboxylates as described hereinand/or water to form an application mixture.

Having described the invention in detail, it will be apparent thatmodifications and variations are possible without departing from thescope of the invention defined in the appended claims.

EXAMPLES

The following non-limiting examples are provided to further illustratethe present invention. It should be noted that the composition examplesbelow are presented on the basis of the components initially combined toform the reported tank mix or concentrate. The various embodiments ofthe present invention are intended to encompass such initialcompositions as well as any corresponding compositions resulting frominteraction among the components once combined, such as where amonocarboxylic acid salt is formed in situ by combining a monocarboxylicacid with a neutralizing base.

Unless otherwise indicated 2601 used in the below examples includes:

-   -   soybean oil (CAS Registry Number 8001-22-7) in a range of 80% to        95% by weight;    -   poly(oxy-1,2-ethanediyl),        α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- (CAS Registry Number        9004-96-0) in a range of 0.25% to 10% by weight; and    -   octadecanoic acid, 12-hydroxy-, homopolymer, ester with α, α′,        α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)]        (CAS Registry Number 1939051-18-9) in a range of 3% to 50% by        weight.

Unless otherwise indicated 2602 used in the below examples includes:

-   -   methyl ester of soybean oil (CAS Registry Number 67784-80-9) in        a range of 80% to 95% by weight;    -   poly(oxy-1,2-ethanediyl),        α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- (CAS Registry Number        9004-96-0) in a range of 0.25% to 10% by weight; and    -   octadecanoic acid, 12-hydroxy-, homopolymer, ester with α, α′,        α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)]        (CAS Registry Number 1939051-18-9) in a range of 3% to 50% by        weight.

Example 1—Dicamba and 2,4-D Straight-Goods Compositions withoutVaporgrip™

Drift retardant formulations shown in Table 1 were prepared. All thecomponents were combined in a beaker with magnetic stirring.Monoethanolamine (MEA) was added to neutralize the phosphate esters indicamba formulations.

TABLE 1 Auxin Straight-Goods Formulations without Vaporgrip ™Formulation 1-1 Formulation 1-2 Formulation 1-3 (26.5% dicamba a.e.)(9.3% dicamba a.e.) (37.5% 2,4-D a.e.) Dicamba 234 g  Dicamba 831 g 2,4-D DMA 334 g (Xtendimax) (Xtend) 2601 16 g  2602 19 g 2602  16 gCrodafos SG 5 g Tryfac 5560-A 25 g MEA 1 g MEA  4 g

Spray particle sizes studies were conducted for these formulations, allof which had drift retardant concentrations which provided 2 oz/ac ratesin the spray tank (FIGS. 1A-B). All data collected is for 1120/560 g/haae at 10 gallons (37.8541 liter) per acre (ac, 0.404686 ha). Particlesize data is from the Q164 Spray Particle Size Facility on six '05nozzles at 40 psi. Formulation 1-3 and Formulation 1-1 built-informulations were tank-mixed with Roundup Powermax®. All tank mixtureswere prepared to deliver 560/1120 g/ha ae dicamba/glyphosate at 10gallons/acre.

It was found that on most nozzles, 2 oz/ac 2601 built into Formulation1-1 tank-mixed with Roundup Powermax®, provides suppression of driftablefines (volume %<150 μm) that is equivalent to the high rate ofInterlock®. The Wilger DR 11005 and Greenleaf TDXL 11005 nozzles usedwith Formulation 1-1 at 40 psi provide fines as low as the TTI 11005nozzle at the same pressure with Xtendimax/Powermax®. At 2 oz/ac, 2602also provides significant reductions in driftable fines, but 2601 issomewhat more effective at this rate. Unlike polymeric drift agents, theemulsion drift agents have little effect on the volume-weighted averageparticle size Dv50 (also known as VMD).

Example 2—Compositions with TEA Salt of 2,4-D and DRAs

Conventional emulsions of drift retardants in TEA salt of 2,4-D weredeveloped based on a 39.4% a.e. solution of the salt, TEA, 2,4-D, asshown in Table 2 below. Three formulations were developed which showedgood physical stability.

TABLE 2 2,4-D TEA Compositions with DRAs Composition CompositionComposition 2-1, 2-2, 2-3, Components 34.1% a.e. 36.5% a.e. 36.0% a.e.TEA, 2,4-D 88.2%   94.2% 93%  2601 4.8%  — — 2602 —  4.8% — Steposol ME— — 5% Break-thru DA 647 2% — — Water 5% — — Toximul 8242 —   1% 2%

Example 3—Dicamba Straight-Goods Compositions with Vaporgrip™

Compositions 3-1 and 3-2 were prepared (Table 3) from dicamba stocksolution which was combined with drift retardant followed by addition ofdispersants and the mixture was agitated at 10 krpm for about 15 secondswith a turrax high-shear mixer.

TABLE 3 Dicamba Compositions with DRA and Vaporgrip ™ CompositionComposition Components 3-1 3-2 Dicamba stock solution 46.6% 53.6% (MEAdicamba, 55% ae) Acetic acid 5.3% 8.2% Potassium hydroxide, 8.9% 12.7%45% wt/wt 2601 6.0% 6.2% Crodafos T6A 2.0% 2.1% Agnique PG 8105 1.0%1.05% SAG 1572 0.01% — Deionized water 30.2% 16.3% 26.1%-dicamba a.e.,30.0% dicamba a.e, pH 5.8, 2.56 lb/gal dicamba a.e. (307 g/L)

TABLE 4 Straight-goods Dicamba Compositions with High-LoadingVaporgrip ™ Composition Composition Composition Components 4-1 4-2 4-3Dicamba stock 47.3%  47.3%  41.8%  solution (MEA dicamba, 55% ae) Aceticacid 14.1%  14.1%  14.7%  45% wt/wt KOH 21.9%  27.8%  29.0%  2601 5.5%5.5% 5.0% Crodafos O3A — 0.5% 0.5% Agnique PG 8105 1.0% 1.4% 1.4% Fastwetter^(†) 0.8% SLES 0.3% A65N 0.3% A65N Castor ethoxylate* 0.5% 82410.8% 8243 0.8% 8241 DI water 8.9% 2.3% 6.5% Dicamba ae  26%  26%  23%

TABLE 5 Comparison of Compositions in Table 4 with Compositions in Table3 Composition Composition Composition Composition 4-1 4-2 4-3 3-2Xtendimax Counterion MEA MEA MEA MEA DGA Dicamba ae  26%  26%  23%  30%29% Dicamba g/L 319 g/L 325 g/L 285 g/L 360 g/L 349 g/L Drift retardant,5.5%, 5.5%, 5.0%, 6.2%, — 2601 1.69 oz/ac 1.69 oz/ac 1.74 oz/ac 1.65oz/ac Total surfactant 2.3% 3.0% 3.0% 3.2% — Acetic 2.0 2.0 2.4 1.0 0.75 acid:dicamb^(†) K-acetate:dicamba^(†) 1.5 1.9 2.2 0.75 0.58

Example 4—Humidome Studies

Compositions 4-1, 4-2, and 4-3 were submitted for humidome studies astank mixtures with Roundup Powermax® I and with Liberty®. Xtendimax(Xmax)-Powermax (PMax) with and without a potassium acetate tank-mixadjuvant were used as controls. The new 1⅛ lb glyphosate rate was usedwith Roundup Powermax® I and the 34-oz rate of Liberty®. The results areshown in Table 6 and FIG. 2A-B. The data in Table 10 shows that theVaporgrip™ levels in Compositions 4-2 and 4-3 reduce the volatility ofhigh-rate Liberty® tank mixtures to the level of the gold standardXmax-Pmax-potassium acetate tank mixture. With Powermax® I, neitherformulation reaches that level, but both reduce dicamba volatility byroughly an order of magnitude over that typically seen withXtendimax-Powermax in this assay, 0.2-0.5 ng/L (not run in thisexperiment).

TABLE 6 Dicamba Volatility, Expressed as an Average Air Concentrationover 24-Hour Period Tank mix Dicamba, ng/L Xmax-Pmax- potassium acetate0.004 Composition 4-1-Pmax 0.056 Composition 4-2-Pmax 0.030 Composition4-3-PMax 0.015 Xmax-Liberty 0.593 Composition 4-1-Liberty 0.025Composition 4-2-Liberty 0.005 Composition 4-3-Liberty 0.004

TABLE 7 Variants of Composition 4-2 with Improved EmulsificationComposition Component 4-2 VM YM Dicamba stock solution 47.3% 48.3% 48.3%(MEA dicamba, 55% ae) Acetic Acid, EMD 14.1% 14.1% 14.1% KOH (45% w/w)27.8% 27.8% 27.8% 2601  5.5%  5.5%  5.5% Crodafos O3A  0.5%  0.5%  0.5%Agnique PG 8105  1.4%  1.5%  1.5% Fast wetter (Lutensol 0.3% A65N 0.2%XL60 0.2% XL60 A65N or Lutensol XL-60) Toximul 8241 or 8243 0.8% 82430.5% 8241 — Pluronic L64 —  0.5%  1.0% DI Water  2.3%  1.1%  1.1%Dicamba ae 26.0% 26.6% 26.6%

The dicamba straight goods formulations, particularly Composition 4-2,provides excellent control of drift and volatility.

Example 5—Premixes of Dicamba-Glyphosate with Vaporgrip™

Base Formulation 8-1 containing dicamba:acetic acid 1:1.5 mol:mol wasprepared for emulsifying drift agents as shown in table below.

TABLE 8 Formulation 8-1 Formulation 8-1 MEA dicamba, 21.36% 56.19% ae(12% ae) MEA glyphosate, 53.57% 44.8% ae (24% ae) Acetic acid  4.89% 45%KOH  7.64% Water 12.54%

Example 6—Greenhouse Testing

A series of formulations GO5, JO3, JO5, EO5, IO5 were prepared by takingcomponents as shown in Table 9 and adding a balance of base Formulation8-1 shown in Table 8. Greenhouse testing for ELEIN control at half-rate(560-280 g/ha a.e. glyphosate-dicamba) are shown.

TABLE 9 Control of goosegrass (ELEIN) at 560-280g/ha a.e.glyphosate-dicamba with formulations containing 2602 dispersed withphosphate esters Formulation GO5 JO3 JO5 EO5 I05 RUP/Xmax Xtend 2602 2.5%  2.5%  2.5%  2.5%  2.5% — — Crodafos 2% O5 2% O3 2% O5 3% O5 4% O5— — PG 264 — 1% 1% — — — — Water added  10%   5% 5% 5% 10% — — (Includes0.5% 50% KOH) ELEIN % control 59.2% 74.2% 74.2% 67.5% 75.0% 96.5% 98.0%

Example 7—Preparation of Formulations with Increased Amounts ofSurfactant

Formulations with increased levels of Crodafos O5A and Agnique PG 264were also prepared. A series of formulations '531, '541, '551, '522,'532, '542, '523, '533, '524, '525 were prepared by taking components asshown in Table 10 and adding a balance of base Formulation 8-1 (MEAdicamba, 56.19% ae+MEA glyphosate, 44.8% ae) micro-emulsified overnightat room temperature and 54° C. with and without 5% water added as shownin table below.

TABLE 10 Formulations with increased Crodafos O5A and Agnique PG 264Formulation ID ‘531 ‘541 ‘551 ‘522 ‘532 ‘542 ‘523 ‘533 ‘524 ‘525 26022.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% 2.5% Crodafos O5A   3%   4%  5%   2%   3%   4%   2%   3%   2%   2% Agnique PG 264   1%   1%   1%  2%   2%   2%   3%   3%   4%   5% Microemulsion^(†) ~ ✓ ✓

✓ ✓

✓

TABLE 11 Specific gravity and loading of dicamba-glyphosate-Vaporgrip ™formulations Dicamba Glyph. wt % wt % Spec. Dic. Loading Gly. LoadingFormulation a.e. a.e. Grav. g/L lb/gal g /L lb/gal ‘541 11.10% 22.20%1.2458 138.28 1.15 276.57 2.31 ‘551 10.98% 21.96% 1.2441 136.60 1.14273.20 2.28 ‘542 10.98% 21.96% 1.2441 136.60 1.14 273.20 2.28 ‘53310.98% 21.96% 1.2453 136.73 1.14 273.47 2.28

TABLE 12 Premix formulation ′542 Formulation ′542, MEA dicamba/ MEAglyphosate, 11.0%/22.0% ae MEA dicamba, 56% a.e. 19.5% 44.8% a.e. MEAglyphosate 49.0% Acetic acid  4.5% 45% KOH  7.0% 2602  2.5% Crodafos O5A 4.0% Agnique PG 264  2.0% Water 11.5%

TABLE 13 High-Vaporgrip ™ formulation, Formulations 13-1 and 13-2Formulation 13-1, Formulation 13-2, MEA dicamba/ MEA dicamba/ MEAglyphosate, MEA glyphosate, 9.5%/21.7% ae, 3.5:1 9.5%/21.7% ae, 3:1Vaporgrip ™:dicamba Vaporgrip ™:dicamba (mol:mol) (mol:mol) Dicambastock solution 17.3% 17.27% (MEA dicamba, 55% ae) 45% a.e. MEAglyphosate 47.6% 47.59% Acetic acid  9.0%  7.74% 45% KOH 14.2% 12.11%2602  2.5%  2.50% Crodafos O5A  4.1%  4.10% Agnique PG 264  2.1%  2.05%Fe dopant (4.5% Fe) 0.41%  0.41% SAG 1572 0.01%  0.01% 1% FD&C 1 BlueDye  0.5%  0.5% Water  2.4%  5.72%

Table 13 shows Formulation 13-1, which features a 3.5:1 aceticacid:dicamba ratio with 9.5%/21.7% dicamba/glyphosate a.e., includes adye, an antifoam (SAG 1572) and an iron safener.

Example 8—Premixes of Dicamba-Glufosinate with Vaporgrip™

Ammonium glufosinate was dissolved into water and stirred followed byaddition of potassium acetate, stir to dissolve. Added 55% a.e. MEAdicamba together with drift reduction agent 2602 and emulsifier,Crodafos and stirred until homogenous. Added surfactant and stirred forat least 20 minutes.

TABLE 14 Dicamba-glufosinate formulations with Vaporgrip and DRAs Formu-Formu- Formu- lation 14-1 lation 14-2 lation 14-3 Ingredients (wt %) (wt%) (wt %) ammonium glufosinate  17.5%  15.8%  17.5% (100%) Dicamba stocksolution 27.17% 24.45% 27.17% (MEA dicamba, 54.58% ae) Potassium acetate16.38% 14.74% 16.38% 2602  5.00%  4.50%  5.00% Crodafos O5A  6.67% 6.00%  6.67% Adsee C80W —  1.80% — APG 264 — —  6.00% water  27.3% 32.8%  21.3% Total 100.0% 100.0% 100.0% Glufosinate:Dicamba % active =% active = % active = 1.0625:1,  32.3%  29.1%  32.3% dicamba:VG-1:2.5total

TABLE 15 Dicamba-glufosinate formulations with Vaporgrip and DRAsFormulations 15-6 15-5 15-4 15-3 15-2 15-1 Ingredients (wt %) (wt %) (wt%) (wt %) (wt %) (wt %) ammonium  17.5%  15.8%  17.5%  17.5%  15.8% 17.5% glufosinate (100%) Dicamba stock 27.17% 24.45% 27.17% 27.17%24.45% 27.17% solution (MEA dicamba, 54.58% ae) Potassium 16.38% 14.74%16.38% 16.38% 14.74% 16.38% acetate 2602  5.00%  4.50%  5.00%  5.00% 4.50%  5.00% Crodafos  6.67%  6.00%  6.67%  6.67%   6.0%  6.67% O4A/O3A(O4A) (O4A) (O4A) (O3A) (O3A) (O3A) APG 264 6.00% — — 6.0% — — AdseeC80W — 1.80% -— —  1.80% — water 21.28%  32.8%  27.3%  21.28%  32.8% 27.3% Total   100%   100%   100%   100%   100%   100% Glufosinate: %active = % active = % active = % active = % active = % active = Dicamba 32.3%  29.1%  32.3%  32.3%  29.1%  32.3% 1.0625: 1, dicamba:VG - 1:2.5

TABLE 16 Dicamba-glufosinate formulations with Vaporgrip and driftretardants Formulations Ingredients 16-1 16-2 16-3 16-4 16-5 Ammonium  21%  19.3%  17.5%  15.8%  17.5% Glufosinate a.i. a.i. a.i. a.i. a.i.MEA 17.8%  16.3%  14.8%  13.4%  14.8% Dicamba a.e. a.e. a.e. a.e. a.e.KOH  6.3%  9.6% — — — AcOH 7.25% 11.07% — — — Potassium — — 16.38%14.74% 16.38% acetate Adsee  4.2%  3.9%  1.8% C80W Crodafos — —  6.7% 6.0%  6.7% O5A 2602 — —  5.0%  4.5%  5.0% APG 264 — — — —  6.0%

Example 9—Weed Efficacy Studies

A. Premixes of Dicamba-Glyphosate with Vaporgrip™

Greenhouse Study:

The efficacy of Formulations '541, '551, '542 and '533 (see Table 11) vsPowermax/Xtendimax and 1st-generation Roundup Xtend was evaluated onELEIN and ABUTH Table 18). The efficacy of pre-mix formulations usingTDXL and TTI nozzles was also tested. All standards including RoundupXtend, Enlist Duo and tank-mix treatments were sprayed using TTI nozzleonly, while pre-mix formulations were sprayed with both TTI and TDXLnozzles. The application rate was 560/1120 g/ha ae dicamba/glyphosate.The comparator formulation is potassium glyphosate without anyadjuvants. Overall, the four pre-mix formulations performed very wellcompared to Roundup Xtend and PowerMax+Xtendimax tank-mix. Nosignificant differences were observed between pre-mix formulations usingthe TTI and TEDx nozzle. On average, TTI was numerically better thanTDXL in most cases. Formulation '541, with lower surfactant, was weakeragainst weeds, but the other three formulations were equivalent to eachother and to a Powermax/Xtendimax control.

Field Study:

Field experiments, or trials, were conducted at 16 Monsanto fieldlocations. A group unbalanced block (GUBD) design with threereplications was used, with a power of greater than 80%, and equivalencetesting with a lower equivalence bound of −10, a delta of <5 when theLSD=5 was used to evaluate. Field preparation during each year consistedof a fall disking followed by a spring disking. In addition to springdisking, if there was a native weed population, a burndown chemistrywith no residual was applied at label rate for the field to start clean,and make sure any native weed bank was at the same growth stage as theplanted in weed species. Weed seeds (4 broadleaf and 4 grasses, speciesdependent on location) were planted to plots measuring 10 by 20 ft.Herbicide treatments were applied using a CO₂ pressurized backpacksprayer or a precision multi-boom sprayer fitted with Teejet TTI110015nozzles, at 15 GPS, when weeds measured 4-7 inches high. In all trials,visual weed control or growth inhibition ratings were recorded at 14 and21 days after treatment (DAT) for each weed species on a 0 to 100% scalewhere 0=no control or growth inhibition and 100=plant death. Data wereanalyzed across different weed species with in each weed group i.e.broadleaf weeds and grasses. Trials and replications within trial wereconsidered random effects and herbicide treatments were considered fixedeffects.

Across 16 locations, 20 treatments, including tank mixes and 0.5× rates,were evaluated for percent control of broadleaf and grass control asshown in Table 18. Entries 1-4 (dicamba alone controls) targeting onlybroadleaves, showed no significant difference in average control ofbroadleaves among the 4 treatments. No significant activity for averagepercent control of the entries 1-4 is seen on grasses. Entries 5 and 6(glyphosate alone controls) were not significantly different betweentreatments on broadleaf or grasses. Entries 7-14 (premix and tank mixesof dicamba and glyphosate) were not significantly different from eachother in average broadleaf control and were equivalent to the commercialtank mix check of Xtendimax plus Roundup Powermax plus Intact. Whenlooking at an individual species level, on broadleaf species, the onlydifference in equivalence is Formulation '541, which is significantlylower in control of redroot pigweed at the full rate, however, whenapplied at the half X rate, it was equivalent of all other treatments.On individual grass leaf species, the only significant difference is thecommercial control with the tank mix of Xtendimax plus Roundup Powermaxplus Intact had much lower control of Proso millet. Half X rates wereused to try to further separate between treatments, however, all 0.5×entries (15-20) were equivalent to each other in both broadleaf andgrass control.

TABLE 17 Efficacy (% control) of Glyphosate + Dicamba Pre-mixFormulations with Built-in DRA Loading Trt. Formulation (%) Rate UnitVolume Unit Nozzle ABUTH ELEIN 1 Roundup Xtend 19.8 560 g ae/ha 15 gal/ATTI 80.8 91.7 2 Roundup Xtend 19.8 1120 g ae/ha 15 gal/A TTI 99.2 97.5 3Roundup 39.8 560 g ae/ha 15 gal/A TTI 82.5 90.8 Powermax 3 XTENDIMAX29.0 280 g ae/ha 15 gal/A TTI 4 INTACT 100.0 0.5 % v/v 15 gal/A TTI 85.087.5 4 Roundup 39.8 560 g ae/ha 15 gal/A TTI Powermax 4 XTENDIMAX 29.0280 g ae/ha 15 gal/A TTI 5 Roundup 39.8 1120 g ae/ha 15 gal/A TTI 96.094.2 Powermax 5 XTENDIMAX 29.0 560 g ae/ha 15 gal/A TTI 6 INTACT 100.00.5 % v/v 15 gal/A TTI 100.0 95.0 6 Roundup 39.8 1120 g ae/ha 15 gal/ATTI Powermax 6 XTENDIMAX 29.0 560 g ac/ha 15 gal/A TTI 7 K-glyphosate48.2 560 g ae/ha 15 gal/A TTI 75.8 40.8 7 XTENDIMAX 29.0 280 g ae/ha 15gal/A TTI 8 K-glyphosate 48.2 1120 g ae/ha 15 gal/A TTI 90.0 84.2 8XTENDIMAX 29.0 560 g ae/ha 15 gal/A TTI 9 Enlist Duo 31.4 420 g ae/ha 15gal/A TDXL 72.5 40.0 10 Enlist Duo 31.4 840 g ae/ha 15 gal/A TDXL 98.880.8 11 Formulation ‘541 22.2 560 g ae/ha 15 gal/A TDXL 75.0 70.0 12Formulation ‘541 22.2 560 g ae/ha 15 gal/A TTI 79.2 84.2 13 Formulation‘541 22.2 1120 g ae/ha 15 gal/A TDXL 93.8 90.0 14 Formulation ‘541 22.21120 g ae/ha 15 gal/A TTI 100.0 92.5 15 Formulation ‘551 22.0 560 gac/ha 15 gal/A TDXL 80.0 77.5 16 Formulation ‘551 22.0 560 g ac/ha 15gal/A TTI 84.2 83.3 17 Formulation ‘551 22.0 1120 g ae/ha 15 gal/A TDXL95.0 91.7 18 Formulation ‘551 22.0 1120 g ae/ha 15 gal/A TTI 100.0 94.219 Formulation ‘542 22.0 560 g ae/ha 15 gal/A TDXL 76.7 79.2 20Formulation ‘542 22.0 560 g ae/ha 15 gal/A TTI 79.2 83.3 21 Formulation‘542 22.0 1120 g ae/ha 15 gal/A TDXL 97.5 93.8 22 Formulation ‘542 22.01120 g ae/ha 15 gal/A TTI 98.8 90.0 23 Formulation ‘533 22.0 560 g ac/ha15 gal/A TDXL 82.5 80.0 24 Formulation ‘533 22.0 560 g ac/ha 15 gal/ATTI 81.7 82.5 25 Formulation ‘533 22.0 1120 g ae/ha 15 gal/A TDXL 97.589.2 26 Formulation ‘533 22.0 1120 g ae/ha 15 gal/A TTI 97.2 93.3

TABLE 18 Average Post-Emergence Broadleaf Control at 21 DAT forBroadleaf and Grass control. Percent Percent Commercial Name orBroadleaf Grass Entry Formulation # AI Rate Applied Control Control  1Xtendimax 0.5 AE #/A 82  7  2 Xtendimax + Intact 0.5 AE #/A + 79  4 0.5%V/V  3 1:1 MEA Dicamba + 0.5 AE #/A 78  3 TBA Dicamba  4 Composition 3-20.5 AE #/A 79  5  5 K-glyphosate 1.125 AE #/A 84 94  6 Roundup Powermax1.125 AE #/A 85 97  7 Xtendimax + 0.5 AE #/A + 96 93 K-glyphosate 1.125AE #/A  8 Xtendimax + Roundup 0.5 AE #/A + 94 95 Powermax + Intact 1.125AE #/A + 0.5% V/V  9 (1:1 MEA Dicamba + 0.5 AE #/A + 95 98 TBADicamba) + 1.125 AE #/A + Roundup Powermax + 0.5% V/V Intact 10Composition 3-2 + 0.5 AE #/A + 95 99 Roundup Powermax 1.125 AE #/A 11Formulation ′541 1.5 AI #/A 93 94 12 Formulation ′551 1.5 AI #/A 95 9613 Formulation ′542 1.5 AI #/A 95 97 14 Formulation ′533 1.5 AI #/A 9095 15* Xtendimax + 0.25 AE #/A + 89 89 K-glyphosate 0.625 AE #/A 16*Xtendimax + Roundup 0.25 AE #/A + 89 96 Powermax + Intact 0.625 AE #/A +0.5% V/V 17* Formulation ′541 0.75 AI #/A 87 92 18* Formulation ′5510.75 AI #/A 87 94 19* Formulation ′542 0.75 AI #/A 87 89 20* Formulation′533 0.75 AI #/A 87 89 Broadleaf species: CHEAL, AMATA, IPOHE, IPOSS,IPOLA, AMASS, AMARE, SIDSP, ABUTH Grass species: ECHCG, DIGSA, PANDI,SETFA, PANMI, BRAPP *0.5X rates

TABLE 19 Greenhouse efficacy data for glufosinate/dicamba formulationsin ABUTH, AMAPA, and PANMI. Loading Rate Trt Formulation (%) (gae/haABUTH AMAPA PANMI  1 XTENDIMAX 29 140 53.3 82.5 0.0  2 XTENDIMAX 29 28081.3 97.5 0.0  3 XTENDIMAX 29 560 87.5 97.5 0.0  4 NPAK AMS 100 2.5 24.222.5 0.0  4 LIBERTY 24.5 165  5 NPAK AMS 100 2.5 42.5 49.2 24.2  5LIBERTY 24.5 330  6 NPAK AMS 100 2.5 69.8 86.7 80.8  6 LIBERTY 24.5 660 7 XTENDIMAX 29 140 75.8 40.0 5.8  7 LIBERTY 24.5 165  8 LIBERTY 24.5330 74.2 66.7 65.5  8 XTENDIMAX 29 280  9 XTENDIMAX 29 560 78.3 99.794.0  9 LIBERTY 24.5 660 10 ENLIST_ONE 38 210 30.8 70.8 0.0 11ENLIST_ONE 38 420 71.7 84.2 1.7 12 ENLIST_ONE 38 840 95.0 99.5 7.5 13LIBERTY 24.5 165 78.3 67.5 18.3 13 ENLIST_ONE 38 210 14 LIBERTY 24.5 33084.7 86.7 63.8 14 ENLIST_ONE 38 420 15 LIBERTY 24.5 660 89.7 90.0 90.715 ENLIST_ONE 38 840 16 Formulation 21 165 71.7 40.8 0.0 16-1 17Formulation 21 330 72.2 59.2 54.2 16-1 18 Formulation 21 660 77.5 94.297.5 16-1 19 Formulation 19.3 165 74.2 49.2 2.5 16-2 20 Formulation 19.3330 74.2 60.0 63.3 16-2 21 Formulation 19.3 660 71.7 96.3 84.2 16-2 22Formulation 17.5 165 67.5 47.5 1.7 16-3 23 Formulation 17.5 330 76.865.0 12.5 16-3 24 Formulation 17.5 660 72.5 92.5 65.0 16-3 25Formulation 15.8 165 65.8 54.2 0.0 16-4 26 Formulation 15.8 330 75.563.3 10.8 16-4 27 Formulation 15.8 660 75.8 93.3 70.0 16-4 28Formulation 17.5 165 67.5 55.8 0.0 16-5 29 Formulation 17.5 330 71.769.2 12.5 16-5 30 Formulation 17.5 660 78.3 100.0 79.2 16-5 Nozzle -TTI110015, Volume - 140 L/ha

TABLE 20 Greenhouse Crop Safety data for glufosinate/dicambaformulations in GLXMA and GOSHI. Rate % INJURY % INJURY (g ai/ha (8DAT)(7DAT) Loading or % GLXMA GOSHI Trt Formulations (%) v/v*) HT3 Soy BG2XF1 LIBERTY 24.5 660 16.7 20.0 2 LIBERTY 24.5 1320 18.2 20.0 3 NPAK_AMS100 2.5* 8.8 18.3 3 LIBERTY 24.5 660 4 NPAK_AMS 100 2.5* 14.3 19.2 4LIBERTY 24.5 1320 5 XTENDIMAX 29 560 0.3 1.7 6 XTENDIMAX 29 1120 2.3 4.27 ROUNDUP_POWERMAX 39.8 1260 3.3 11.3 8 ROUNDUP_POWERMAX 39.8 2520 6.213.3 9 XTENDIMAX 29 560 5.2 4.2 9 LIBERTY 24.5 660 10 XTENDIMAX 29 112012.8 5.2 10 LIBERTY 24.5 1320 11 LIBERTY 24.5 660 8.8 4.5 11 XTENDIMAX29 560 11 ROUNDUP_POWERMAX 39.8 1260 12 LIBERTY 24.5 1320 17.5 11.3 12XTENDIMAX 29 1120 12 ROUNDUP_POWERMAX 39.8 2520 13 Formulation 16-1 21660 1.2 0.3 14 Formulation 16-1 21 1320 9.3 4.5 15 Formulation 16-2 19.3660 2.5 0.0 16 Formulation 16-2 19.3 1320 10.2 1.2 17 Formulation 16-317.5 660 0.5 0.8 18 Formulation 16-3 17.5 1320 7.3 5.3 19 Formulation16-4 15.8 660 1.5 1.3 20 Formulation 16-4 15.8 1320 7.7 5.8 21Formulation 16-5 17.5 660 0.8 0.8 22 Formulation 16-5 17.5 1320 5.2 4.023 ROUNDUP_POWERMAX 39.8 1260 9.0 4.3 23 Formulation 16-1 21 660 24ROUNDUP_POWERMAX 39.8 2520 18.3 9.8 24 Formulation 16-1 21 1320 25Formulation 16-2 19.3 660 9.3 2.0 25 ROUNDUP_POWERMAX 39.8 1260 26Formulation 16-2 19.3 1320 15.8 10.2 26 ROUNDUP_POWERMAX 39.8 2520 27ROUNDUP_POWERMAX 39.8 1260 7.5 3.7 27 Formulation 16-3 17.5 660 28Formulation 16-3 17.5 1320 13.0 12.0 28 ROUNDUP_POWERMAX 39.8 2520 29ROUNDUP_POWERMAX 39.8 1260 10.2 4.2 29 Formulation 16-4 15.8 660 30ROUNDUP_POWERMAX 39.8 2520 17.8 15.0 30 Formulation 16-4 15.8 1320 31Formulation 16-5 17.5 660 7.7 2.5 31 ROUNDUP_POWERMAX 39.8 1260 32Formulation 16-5 17.5 1320 15.0 11.0 32 ROUNDUP_POWERMAX 39.8 2520Nozzle-TTI110015, Volume-140 L/ha

Example 10—Dicamba Microemulsion Compositions with DRA and Vaporgrip™

Acetic acid and potassium hydroxide were mixed in given ratios followedby addition of other ingredients in no specific order to providemicroemulsion compositions shown below in Tables 21-26.

TABLE 21 Dicamba Microemulsion Compositions with DRA and 1:1Vaporgrip™:DicambaRatio Composition Ingredients 21-1 21-2 21-3 21-4 21-521-6 Dicamba stock 65.35% 65.35% 65.37% 60.00% 61.00% — solution (MEAdicamba, 55.08% ae) Acetic Acid 9.78% 9.78% 9.78% 8.98% 9.13% — KOH 45%w/w 15.20% 15.20% 15.20% 13.96% 14.19% — Drift Retardant 6.31% 6.29%6.29% — — — 2601 Drift Retardant — — — 6.06% 6.16% 6.07% 2602 SurfonicL2-6 3.36% 2.77% 1.20% — 2.80% 0.91% AGM 550 — 0.61% 2.16% — — 1.21%n-Decanol — — — 6.61% 6.72% — Ethomeen C/12 — — — 4.41% — 5.70%Propylene — — — — — 33.75% Glycol Dicamba Tech — — — — — 29.63% (98.30%ae) Sodium — — — — — 8.95% Formate DI Water — — — — — 13.78% Total100.00% 100.00% 100.00% 100.00% 100.00% 100.00%

TABLE 22 Dicamba Microemulsion Compositions with DRA and 1.5:3.0Vaporgrip™M : Dicamba Ratio Composition Ingredients 22-1 22-2 22-3 22-422-5 22-6 Vapor Grip:Dicamba 1.5:1 1.75:1 2:1 2.5:1 2.8:1 3:1 Dicambastock 54.19% 53.69% 48.58% 46.85% 43.87% 35.88% solution (MEA dicamba,55.08% ae) Acetic Acid 12.17% 14.06% 14.79% 14.89% 9.13% 16.10% KOH 45%w/w 18.91% 21.85% 22.99% 23.14% 14.19% 25.03% Drift Retardant 2602 6.17%3.99% 5.18% 4.77% 4.24% — Drift Retardant 2601 — — — 4.08% Surfonic L2-62.40% 0.49% 0.91% 1.30% 2.11% n-Decanol 6.17 5.92 7.71 9.05% 9.87% 3.95%Decane — — — — — 3.75% Ethomeen C/12 — — — — — 11.20% Total 100.00%100.00% 100.00% 100.00% 100.00% 100.00%

TABLE 23 Dicamba Microemulsion Compositions with DRA and 2:1Vaporgrip ™:Dicamba Ratio Vapor Grip:Dicamba 2:1 2:1 2:1 2:1 Sample IDComposition Composition Composition Composition Ingredients 23-1 23-223-3 23-4 Dicamba stock  49.84% — — — solution (MEA dicamba, 55.08% ae)MEA dicamba —  47.83%  47.93%  47.93% (62.58% ae) Acetic Acid  14.90% 16.25%  16.29%  16.29% KOH 45% w/w  23.17%  25.35%  25.32%  25.32%Drift  6.50%  6.51%  6.50%  6.50% Retardant 2601 Emulpon  2.65%  1.85% 2.56%  0.83% CO-550 Crodafos T6A  1.28%  1.02%  0.13%  1.85% Decane 1.65%  1.28%  1.28%  1.28% FD&C Blue 1  0.005% —  0.005% — Total100.00% 100.00% 100.00% 100.00%

TABLE 24 Dicamba Microemulsion Compositions with DRA and 0:1-2:1Vaporgrip ™:Dicamba Ratio Vapor Grip:Dicamba 2:1 2:1 2:1 2:1 Sample IDComposition Composition Composition Composition Ingredients 24-1 24-224-3 24-4 Dicamba stock  46.28%  44.08%  46.26%  69.09% solution (MEAdicamba, 56.20% ae) Acetic Acid  14.12%  13.45%  14.11% — KOH 45% w/w 21.95%  20.91%  21.94% — Drift  6.50%  6.28%  6.50%  6.34% Retardant2601 Surfom R 540  2.56% — — — Emulpon —  2.48  2.51% — CO-550 CrodafosT6A  1.65% —  0.87% — Crop Oil —  3.47% — — Concentrate Conosol C-170 6.94%  9.33%  7.80% — TAC — — —  8.21% Surfonic L12-3 — — —  6.22% DIWater — — —  10.15% FD&C Blue  0.005%  0.005% 0.005 — Total 100.00%100.00% 100.00% 100.00%

TABLE 25 Dicamba Microemulsion Compositions with DRA and 2-4Vaporgrip ™:Dicamba Vapor Grip:Dicamba 2:1 2:1 3:1 4:1 Sample IDComposition Composition Composition Composition Ingredients 25-1 25-225-3 25-4 Dicamba stock  46.29%  46.33%  37.96% — solution (MEA dicamba,56.20% ae) Dicamba stock — — —  33.93% solution (MEA dicamba, 55.98% ae)Acetic Acid  14.13%  14.15%  17.37%  20.63% KOH 45% w/w  21.97%  21.99% 27.03%  32.22% Drift  5.03%  5.03%  4.12%  4.45% Retardant 2602Crodafos O3A  3.64%  7.20%  5.90%  4.89% Propylene —  5.29%  4.34% 3.88% Glycol Propylene  8.93% — — — Carbonate DI Water — —  3.27% —Total 100.00% 100.00% 100.00% 100.00%

TABLE 26 Dicamba ME Compositions with Methyl Soyate/Soy Bean Oil and 2:1Vaporgrip ™:Dicamba Vapor Grip:Dicamba 2:1 2:1 Sample ID CompositionComposition Ingredients 26-1 26-2 Dicamba stock solution (MEA  46.52% 46.45% dicamba, 55.98% ae) Acetic Acid  14.10%  14.12% KOH 45% w/w 21.91%  21.95% Methyl Soyate  5.02% — Crodafos O3A  7.18% — PropyleneGlycol  5.27% — Soy Bean Oil —  6.43% Emulpon CO-550 —  2.49% CrodafosT6A —  0.86% Conosol C-170 —  7.71% Total 100.00% 100.00%

Example 11—Humidome Volatility of Dicamba Microemulsion Compositionswith DRA and Vaporgrip™

A humidone volatility study was performed as described in U.S. Pat. No.9,743,664, of which its entirety is incorporated herein by reference.The results are shown in Table 27 below.

TABLE 27 Dicamba MEA Compositions with DRA and 2:1 Vapor Grip to Dicambaratio Vapor Grip:Dicamba 2:1 2:1 2:1 2:1 2:1 Sample ID CompositionComposition Composition Composition Composition Ingredients 27-1 27-227-3 27-4 27-5 Dicamba stock  40.57% — — — — solution (MEA dicamba,55.08% ae) Dicamba stock — — — —  48.43% solution (MEA dicamba, 56.20%ae) MEA dicamba —  50.17%  47.83%  48.00% — (62.58% ae) Acetic Acid 12.13%  15.00%  16.25%  16.31%  14.79% KOH 45% w/w  18.84%  23.30% 25.26%  25.35%  22.99% Drift Retardant — — — —  5.18% ERS 2602 DriftRetardant  4.17%  7.18%  6.51%  6.51% — ERS 2601 Emulpon —  2.76%  1.85% 1.54% — CO-550 Crodafos T6A — —  1.02%  1.02% — Surfonic L12-3  2.98% —— — — Surfonic L12-6 — — — —  0.91% n-Decanol — — — —  7.71% Decane 1.19%  1.57%  1.28%  1.28% — Ethomeen C/12  20.11% — — — — Total100.00% 100.00% 100.00% 100.00% 100.00%

TABLE 28 Humidome Volatility of Dicamba Microemulsion with DRA and 2:1to 4:1 Vaporgrip ™:Dicamba Ratio Dicamba, ng/L Vapor Grip:DicambaProduct ID 2:1 3:1 4:1 Composition 23-1 0.000 Composition 23-1-Pmax0.015 Xmax-Pmax- potassium acetate 0.001 Composition 23-2 0.001Composition 23-2-Pmax 0.043 Xmax-Pmax-potassium acetate 0.003Composition 27-2 0.001 Composition 27-2-Pmax 0.043 Xmax-Pmax-potassiumacetate 0.003 Composition 27-5 0.001 Composition 27-5-Pmax 0.031Xmax-Pmax-potassium acetate 0.001 Composition 25-2 0.001 Composition25-2-Pmax 0.070 Xmax-Pmax-potassium acetate 0.002 Composition 25-1 0.001Composition 25-1-Pmax 0.025 Xmax-Pmax-potassium acetate 0.001Composition 24-1 0.001 Composition 24-1-Pmax 0.013 Xmax-Pmax-potassiumacetate 0.004 Composition 25-3 0.000 Composition 25-3-Pmax 0.012Xmax-Pmax-potassium acetate 0.002 Composition 24-2 0.001 Composition24-2-Pmax 0.073 Xmax-Pmax-potassium acetate 0.005 Composition 27-3 0.001Composition 27-4 0.001 Xmax-Pmax-potassium acetate 0.004 Composition27-1 0.000 Composition 22-6 0.000 Xmax-Pmax-potassium acetate 0.003Composition 25-4 0.001 Composition 25-4-Pmax 0.005 Xmax-Pmax-potassiumacetate 0.003

Example 12—2,4-D and Glyphosate Microemulsion Compositions with DRA

Method of preparation: Water and DMAPA (3-(dimethylamino)-1-propylamine)were added to a glass bottle and stirred until homogeneous. Then added2,4-D acid, followed by glyphosate acid wetcake and stirred until fullydissolved. Then Drift Retardant 2602 and surfactant Crodafos™ O5A wereadded and stirred until homogenous solution was obtained. Agnique® PG264/Ethoquad®/Agnique PG8107/AGM 550 were added last and subsequentlystirred for 20 minutes until clear a formulation was obtained. See,Table 29.

TABLE 29 Sample ID Composition Composition Composition CompositionIngredient 05-1 05-4 05-5 05-6 2,4-D Tech  13.5%  15.80%  15.80%  13.50%(98.2%) Glyphosate 20.46%  23.73%  23.73%  20.46% wetcake (97.73%) DMAPA11.22%  13.08%  13.08%  11.22% 2602  2.50%  3.00%  3.00%  2.50% CrodafosO5A  4.00%  3.90%  3.90%  3.00% Ethoquad C12 — —  2.00% — Agnique  2.00% 2.50%  2.50%  2.00% PG 264 Agnique — — —  4.00% PG 8107 AGM 550 — — — 2.00% Water  46.3%  38.0%  36.0%  41.3% Total 100.0% 100.00% 100.00%100.00%

This written description uses examples to disclose the invention,including the best mode, and also to enable any person skilled in theart to practice the invention, including making and using any devices orsystems and performing any incorporated methods. The patentable scope ofthe invention is defined by the claims, and may include other examplesthat occur to those skilled in the art. Such other examples are intendedto be within the scope of the claims if they have structural elementsthat do not differ from the literal language of the claims, or if theyinclude equivalent structural elements with insubstantial differencesfrom the literal languages of the claims.

What is claimed is:
 1. A herbicidal composition concentrate comprising:(a) at least one auxin herbicide; (b) at least one drift retardant agentcomprising a compound of Formula II:

wherein i+j+k=10 to 50 and r+s+t=3 to 12; (c) an emulsifying agentselected from the group consisting of a phosphate ester, analkylpolysaccharide, an alkoxylated castor oil, and a combinationthereof; and, (d) optionally, at least one additional drift retardantagent comprising: soybean oil or a methyl ester of soybean oil; and/or acompound according of Formula I:

wherein n is 50-250.
 2. The herbicidal composition concentrate of claim1, wherein one or more of the following are satisfied: (i) the at leastone auxin herbicide is present in an amount (acid equivalent weight) ofabout 5% to about 50% by weight of the composition concentrate; (ii) theat least one drift retardant agent is present in an amount of about 2%to about 10% by weight of the composition concentrate; and (iii) theemulsifying agent is present in an amount of about 1% to about 20% byweight of the composition concentrate.
 3. The herbicidal compositionconcentrate of claim 1, wherein the at least one drift retardant agentcomprises: a compound of Formula II in an amount of about 3% to about50% by weight of the drift retardant agent.
 4. The herbicidalcomposition concentrate of claim 1, wherein the compound of Formula I ispoly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- andthe compound of Formula II is octadecanoic acid, 12-hydroxy-,homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)] and/or theat least one auxin herbicide is selected from the group consisting ofdicamba, an agriculturally acceptable salt of dicamba, an agriculturallyacceptable ester of dicamba, 2,4-D, an agriculturally acceptable salt of2,4-D, an agriculturally acceptable ester of 2,4-D, and a combinationthereof.
 5. The herbicidal composition concentrate of claim 1, whereinthe at least one auxin herbicide is an agriculturally acceptable salt ofdicamba, wherein the salt is selected from group consisting ofN,N-[aminopropyl]methylamine, monoethanolamine, dimethylamine,isopropylamine, diglycolamine, a potassium salt, and a sodium salt, anda combination thereof.
 6. The herbicidal composition concentrate ofclaim 1, further comprising one or more of: (i) at least onemonocarboxylic acid or a monocarboxylate thereof; and (ii) at least onefurther herbicide.
 7. The herbicidal composition concentrate of claim 6,wherein the at least one monocarboxylic acid or the monocarboxylatethereof is present in an amount (acid equivalent weight) of about 5% toabout 30% by weight of the composition concentrate; and wherein the atleast one further herbicide is present in an amount (acid equivalentweight) of about 10% to about 50% by weight of the compositionconcentrate.
 8. The herbicidal composition concentrate of claim 6,wherein the molar ratio of the at least one monocarboxylic acid or themonocarboxylate thereof to the auxin herbicide is from about 3:10 toabout 10:1.
 9. The herbicidal composition concentrate of claim 6,wherein the monocarboxylic acid is acetic acid or the monocarboxylate ispotassium acetate; and wherein the at least one further herbicide isselected from the group consisting of glyphosate, an agriculturallyacceptable salt of glyphosate, glufosinate, an agriculturally acceptablesalt of glufosinate, and a combination thereof.
 10. The herbicidalcomposition concentrate of claim 1, wherein the composition concentrateis an emulsion or a micro-emulsion.
 11. A method of making an herbicidalcomposition concentrate, the method comprising: admixing at least oneauxin herbicide with at least one drift retardant agent, an emulsifyingagent, and, optionally, at least one additional drift retardant agent,wherein the at least one drift retardant agent comprises a compound ofFormula II:

wherein i+j+k=10 to 50 and r+s+t=3 to 12; wherein the emulsifying agentis selected from the group consisting of a phosphate ester, analkylpolysaccharide, an alkoxylated castor oil, and a combinationthereof to form the herbicidal composition concentrate, and wherein theat least one additional drift retardant agent comprises: soybean oil ora methyl ester of soybean oil; and/or a compound according of Formula I:

wherein n is 50-250.
 12. The method of claim 11, wherein the compositionconcentrate comprises one or more of: (i) the at least one auxinherbicide in an amount (acid equivalent weight) of about 5% to about 50%by weight; (ii) the at least one drift retardant agent in an amount ofabout 2% to about 10% by weight of the composition concentrate; (iii)the emulsifying agent in an amount of about 1% to about 20% by weight ofthe composition concentrate.
 13. The method of claim 11, wherein thecompound of Formula I is poly(oxy-1,2-ethanediyl),α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy- and the compound of FormulaII is octadecanoic acid, 12-hydroxy-, homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)] and/or theat least one auxin herbicide is selected from the group consisting ofdicamba, an agriculturally acceptable salt of dicamba, an agriculturallyacceptable ester of dicamba, 2,4-D, an agriculturally acceptable salt of2,4-D, an agriculturally acceptable ester of 2,4-D, and a combinationthereof.
 14. The method of claim 11, wherein the at least one auxinherbicide is an agriculturally acceptable salt of dicamba, wherein thesalt is selected from group consisting of N,N-[aminopropyl]methylamine,monoethanolamine, dimethylamine, isopropylamine, diglycolamine, apotassium salt, and a sodium salt, and a combination thereof.
 15. Themethod of claim 11, further comprising one or more of: (i) admixing theat least one auxin herbicide with water to form an aqueous solutionprior to admixing with the at least one drift retardant agent and theemulsifying agent; (ii) admixing at least one monocarboxylic acid or amonocarboxylate thereof with the at least one auxin herbicide, the atleast one drift retardant agent, and the emulsifying agent; and (iii)admixing at least one further herbicide with the at least one auxinherbicide, the at least one drift retardant agent, and the emulsifyingagent.
 16. The method of claim 15, wherein the composition concentratecomprises the at least one monocarboxylic acid or the monocarboxylatethereof in an amount (acid equivalent weight) of about 5% to about 30%by weight of the composition concentrate; and wherein the compositionconcentrate comprises the at least one further herbicide in an amount(acid equivalent weight) of about 15% to about 60% by weight of thecomposition concentrate.
 17. The method of claim 15, wherein the molarratio of the at least one monocarboxylic acid or the monocarboxylatethereof to the auxin herbicide is from about 3:10 to about 10:1.
 18. Themethod of claim 15, wherein the monocarboxylic acid is acetic acid orthe monocarboxylate is potassium acetate; and wherein the at least onefurther herbicide is selected from the group consisting of glyphosate,an agriculturally acceptable salt of glyphosate, glufosinate, anagriculturally acceptable salt of glufosinate, and a combinationthereof.
 19. The method of claim 11, wherein the at least one driftretardant agent comprises: a compound of Formula II in an amount ofabout 3% to about 50% by weight of the drift retardant agent.
 20. Adrift retardant agent composition for use in the preparation of aherbicidal application mixture, the drift retardant agent compositioncomprising: (a) at least one drift retardant agent comprising:octadecanoic acid, 12-hydroxy-, homopolymer, ester with α, α′,α″-1,2,3-propanetriyltris[ω-hydroxypoly(oxy-1,2-ethanediyl)]; and (b) anemulsifying agent selected from the group consisting of a phosphateester, alkylpolysaccharide, an alkoxylated castor oil, and a combinationthereof, and, optionally: (c) at least one additional drift retardantagent comprising: soybean oil or a methyl ester of soybean oil; and/orpoly(oxy-1,2-ethanediyl), α-[(9Z)-1-oxo-9-octadecen-1-yl]-ω-hydroxy-.21. The herbicidal composition concentrate of claim 1, wherein the atleast one additional drift retardant agent comprises: soybean oil or amethyl ester of soybean oil in an amount of about 80% to about 95% byweight of the drift retardant agent; and/or a compound of Formula I inan amount of about 0.25% to about 10% by weight of the drift retardantagent.
 22. The method of claim 11, wherein the at least one additionaldrift retardant agent comprises: soybean oil or a methyl ester ofsoybean oil in an amount of about 80% to about 95% by weight of thedrift retardant agent; and/or a compound of Formula I in an amount ofabout 0.25% to about 10% by weight of the drift retardant agent.